CA2218552A1 - Benzimidazole compounds and their use as modulators of the gabaa receptor complex - Google Patents
Benzimidazole compounds and their use as modulators of the gabaa receptor complexInfo
- Publication number
- CA2218552A1 CA2218552A1 CA002218552A CA2218552A CA2218552A1 CA 2218552 A1 CA2218552 A1 CA 2218552A1 CA 002218552 A CA002218552 A CA 002218552A CA 2218552 A CA2218552 A CA 2218552A CA 2218552 A1 CA2218552 A1 CA 2218552A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- disorders
- modulators
- receptor complex
- gabaa receptor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 2
- 102000027484 GABAA receptors Human genes 0.000 title 1
- 108091008681 GABAA receptors Proteins 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 206010010904 Convulsion Diseases 0.000 abstract 1
- 208000026139 Memory disease Diseases 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 206010015037 epilepsy Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 208000019116 sleep disease Diseases 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present patent application discloses compounds having the formula or a pharmaceutically acceptable salt thereof or an oxide thereof wherein R3 is wherein A, B and D each is CH, or one or two of A, B and D is N and the others are CH;
R11 is phenyl, benzimidazolyl, or monocyclic heteroaryl, all of which may be substituted one or more times with substituents selected from alkyl, alkoxy, halogen, CF3, amino, nitro, cyano, acylamino, acyl, phenyl and monocyclic heteroaryl;
one of R6 and R7 is hydrogen and the other is -CR'=NOR", wherein R' and R"
each independently are hydrogen, alkyl, alkenyl, alkynyl or phenyl.
The compounds are useful for the treartment of various central nervous system disorders such as epilepsy and other convulsive disorders, anxiety, sleep disorders and memory disorders.
R11 is phenyl, benzimidazolyl, or monocyclic heteroaryl, all of which may be substituted one or more times with substituents selected from alkyl, alkoxy, halogen, CF3, amino, nitro, cyano, acylamino, acyl, phenyl and monocyclic heteroaryl;
one of R6 and R7 is hydrogen and the other is -CR'=NOR", wherein R' and R"
each independently are hydrogen, alkyl, alkenyl, alkynyl or phenyl.
The compounds are useful for the treartment of various central nervous system disorders such as epilepsy and other convulsive disorders, anxiety, sleep disorders and memory disorders.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK46095 | 1995-04-21 | ||
| DK0460/95 | 1995-04-21 | ||
| DK74195 | 1995-06-27 | ||
| DK0741/95 | 1995-06-27 | ||
| PCT/EP1996/001649 WO1996033191A1 (en) | 1995-04-21 | 1996-04-19 | Benzimidazole compounds and their use as modulators of the gabaa receptor complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2218552A1 true CA2218552A1 (en) | 1996-10-24 |
| CA2218552C CA2218552C (en) | 2002-04-16 |
Family
ID=26064049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002218552A Expired - Fee Related CA2218552C (en) | 1995-04-21 | 1996-04-19 | Benzimidazole compounds and their use as modulators of the gabaa receptor complex |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5922725A (en) |
| EP (1) | EP0821682B1 (en) |
| JP (1) | JP3171852B2 (en) |
| KR (1) | KR100283363B1 (en) |
| CN (1) | CN1089762C (en) |
| AT (1) | ATE194836T1 (en) |
| AU (1) | AU699623B2 (en) |
| BR (1) | BR9608056A (en) |
| CA (1) | CA2218552C (en) |
| CZ (1) | CZ287538B6 (en) |
| DE (1) | DE69609413T2 (en) |
| DK (1) | DK0821682T3 (en) |
| EE (1) | EE04308B1 (en) |
| ES (1) | ES2150671T3 (en) |
| GR (1) | GR3034558T3 (en) |
| HK (1) | HK1018048A1 (en) |
| HU (1) | HU224031B1 (en) |
| IS (1) | IS2020B (en) |
| MX (1) | MX9708147A (en) |
| NO (1) | NO314502B1 (en) |
| NZ (1) | NZ307532A (en) |
| PL (1) | PL184020B1 (en) |
| PT (1) | PT821682E (en) |
| RU (1) | RU2136676C1 (en) |
| SK (1) | SK282105B6 (en) |
| TR (1) | TR199701219T1 (en) |
| UA (1) | UA54394C2 (en) |
| WO (1) | WO1996033191A1 (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69739733D1 (en) | 1996-10-21 | 2010-02-25 | Neurosearch As | 1-PHENYL-BENZIMIDAZOL COMPOUNDS AND THEIR USE AS GABA-A RECEPTOR MODULATORS |
| JP3868502B2 (en) * | 1996-10-25 | 2007-01-17 | ニューロサーチ・アクティーゼルスカブ | Method for identifying compound having anti-anxiety action |
| GB9702524D0 (en) * | 1997-02-07 | 1997-03-26 | Merck Sharp & Dohme | Therapeutic agents |
| JP2001519429A (en) * | 1997-10-10 | 2001-10-23 | ニューロサーチ、アクティーゼルスカブ | Benzimidazole compounds, pharmaceutical compositions containing the compounds, and uses thereof |
| WO1999029319A2 (en) * | 1997-12-09 | 1999-06-17 | Neurosearch A/S | Chemical compounds for use as anxiolytic agents and a method for the identification of anxiolytic compounds |
| AU4652699A (en) * | 1998-07-15 | 2000-02-07 | Meiji Seika Kaisha Ltd. | Process for producing 4-substituted-2-nitro-fluorobenzenes |
| CA2348234A1 (en) * | 1998-10-29 | 2000-05-11 | Chunjian Liu | Compounds derived from an amine nucleus that are inhibitors of impdh enzyme |
| US6627624B1 (en) | 1999-04-02 | 2003-09-30 | Neurogen Corporation | Aryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| US6380210B1 (en) | 1999-04-02 | 2002-04-30 | Neurogen Corporation | Heteroaryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| US6271241B1 (en) | 1999-04-02 | 2001-08-07 | Neurogen Corporation | Cycloalkyl and aryl fused aminoalkyl-imidazole derivatives: modulators and GLP-1 receptors |
| US6281237B1 (en) | 1999-04-02 | 2001-08-28 | Neurogen Corporation | N-phenyl benzimidazolecarboxamide and N-phenyl indolecarboxamide derivatives |
| RU2243226C2 (en) * | 1999-06-22 | 2004-12-27 | НьюроСёрч А/С | New derivatives of benzimidazole and pharmaceutical compositions containing thereof |
| US6642229B2 (en) | 2000-05-24 | 2003-11-04 | Merck Sharp & Dohme Ltd. | 3-Phenyl-imidazo-pyrimidine derivatives as ligands for GABA receptors |
| TWI248936B (en) * | 2001-03-21 | 2006-02-11 | Merck Sharp & Dohme | Imidazo-pyrimidine derivatives as ligands for GABA receptors |
| ATE338758T1 (en) * | 2001-03-23 | 2006-09-15 | Merck Sharp & Dohme | IMIDAZOPYRIMIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS |
| EP1590339A4 (en) * | 2003-01-28 | 2007-07-25 | Smithkline Beecham Corp | Chemical compounds |
| WO2004087690A2 (en) | 2003-04-03 | 2004-10-14 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gaba-a receptor complex |
| EP1613312B1 (en) | 2003-04-03 | 2008-02-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gaba a receptor complex |
| TWI391381B (en) | 2006-03-24 | 2013-04-01 | Neurosearch As | Benzimidazole derivatives, pharmaceutical compositions containing the same, and use of the same for the manufacture of a medicament |
| WO2010055126A1 (en) * | 2008-11-14 | 2010-05-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| WO2011047315A1 (en) | 2009-10-15 | 2011-04-21 | Concert Pharmaceuticals, Inc. | Subsitituted benzimidazoles |
| CN111542520B (en) | 2017-09-28 | 2022-04-15 | 基石药业（苏州）有限公司 | As A2AFused ring derivatives of receptor inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE163290T1 (en) * | 1991-06-24 | 1998-03-15 | Neurosearch As | IMIDAZOLE COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR APPLICATION |
| US5158969A (en) * | 1991-08-21 | 1992-10-27 | Neurosearch A/S | Indole derivatives as potassium channel blockers |
| DK40192D0 (en) * | 1992-03-26 | 1992-03-26 | Neurosearch As | IMIDAZOLE COMPOUNDS, THEIR PREPARATION AND USE |
| AU675484B2 (en) * | 1993-03-24 | 1997-02-06 | Neurosearch A/S | Benzimidazole compounds, their use and preparation |
-
1996
- 1996-04-19 ES ES96914957T patent/ES2150671T3/en not_active Expired - Lifetime
- 1996-04-19 EP EP96914957A patent/EP0821682B1/en not_active Expired - Lifetime
- 1996-04-19 PT PT96914957T patent/PT821682E/en unknown
- 1996-04-19 HU HU9802272A patent/HU224031B1/en not_active IP Right Cessation
- 1996-04-19 NZ NZ307532A patent/NZ307532A/en unknown
- 1996-04-19 CN CN96193421A patent/CN1089762C/en not_active Expired - Fee Related
- 1996-04-19 MX MX9708147A patent/MX9708147A/en not_active IP Right Cessation
- 1996-04-19 UA UA97115592A patent/UA54394C2/en unknown
- 1996-04-19 US US08/945,123 patent/US5922725A/en not_active Expired - Lifetime
- 1996-04-19 JP JP53148496A patent/JP3171852B2/en not_active Expired - Fee Related
- 1996-04-19 AU AU56906/96A patent/AU699623B2/en not_active Ceased
- 1996-04-19 AT AT96914957T patent/ATE194836T1/en not_active IP Right Cessation
- 1996-04-19 CA CA002218552A patent/CA2218552C/en not_active Expired - Fee Related
- 1996-04-19 KR KR1019970707463A patent/KR100283363B1/en not_active IP Right Cessation
- 1996-04-19 EE EE9700282A patent/EE04308B1/en not_active IP Right Cessation
- 1996-04-19 SK SK1406-97A patent/SK282105B6/en unknown
- 1996-04-19 TR TR97/01219T patent/TR199701219T1/en unknown
- 1996-04-19 CZ CZ19973291A patent/CZ287538B6/en not_active IP Right Cessation
- 1996-04-19 BR BR9608056-6A patent/BR9608056A/en not_active IP Right Cessation
- 1996-04-19 WO PCT/EP1996/001649 patent/WO1996033191A1/en active IP Right Grant
- 1996-04-19 RU RU97119174A patent/RU2136676C1/en not_active IP Right Cessation
- 1996-04-19 DE DE69609413T patent/DE69609413T2/en not_active Expired - Lifetime
- 1996-04-19 PL PL96322944A patent/PL184020B1/en not_active IP Right Cessation
- 1996-04-19 DK DK96914957T patent/DK0821682T3/en active
-
1997
- 1997-10-17 IS IS4593A patent/IS2020B/en unknown
- 1997-10-20 NO NO19974843A patent/NO314502B1/en unknown
-
1998
- 1998-10-09 HK HK98111154A patent/HK1018048A1/en not_active IP Right Cessation
-
2000
- 2000-10-04 GR GR20000402248T patent/GR3034558T3/en not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |